Following the trends and looking... more dated?

Hi All, I commented on a post last week about updating the millennial ballet flat and reading some comments has me thinking through trend cycles a lot. Skinny jeans and ballet flats are becoming fresh again. I live pretty rurally and haven't been seeing this in person yet (it's kind of Rudy Jude / workwear world here).

I don't expect that people are just copy pasting the outfits from over a decade ago. But we're still working with those items (for this example, at least).

That's all well and good if you're 20 and you just look trendy. But if I show up in that fit in my 30s I'd expect to look quite dated. So for those who have seen a trend that is deeply associated with your generation come back, what did you do? Embrace it and pull your old looks out of storage? Update it enough for it to not match up with the "dated" version?

I ask this in a kind of abstract way since I have no desire to wear those particular items. I dress a lot more masc than I did in 2014 when I was scrolling dreamily on modcloth. But I do think seeing some comparisons on styling would be interesting if anyone has some!